Cesium carbonate → 9,10-di(2-naphthyl)-2-(2-phenyl-1H-benzimidazol-1-yl)anthracene

HRID 1172782ノート

反応式

HRID 1172782 の反応式
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:36]1([C:42]2[NH:46][C:45]3[CH:47]=[CH:48][CH:49]=[CH:50][C:44]=3[N:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C1C2C(=CC=C3C=2N=NC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cu](I)I>[CH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][C:26]=1[C:5]1[C:4]2[C:13]([C:12]([C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)=[C:11]3[C:6]=1[CH:7]=[C:8]([N:46]1[C:45]4[CH:47]=[CH:48][CH:49]=[CH:50][C:44]=4[N:43]=[C:42]1[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH:9]=[CH:10]3)=[CH:14][CH:15]=[CH:2][CH:3]=2

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 128552-PhenylbenzimidazoleHCID 601987Benzo[h]cinnolineHCID 222471572-Bromo-9,10-di(naphthalen-2-yl)anthracene

生成物 1

HCID 231602259,10-di(2-naphthyl)-2-(2-phenyl-1H-benzimidazol-1-yl)anthracene収率 35.3%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

5.1 g (10 mmol) of 2-bromo-9,10-di(2-naphthyl)anthracene, 2.3 g (12 mmol) of 2-phenyl-1H-benzimidazole, 0.19 g (11.0 mmol) of copper iodide, and 3.6 g (2.0 mmol) of 9,10-phenanthroline were dissolved into a 2 M solution of cesium carbonate in dimethylformamide (DMF), and the whole was refluxed under heating for 48 hours in an argon atmosphere. After the completion of the reaction, the resultant was filtered. The filtrate was poured into 1 L of 10-mass % hydrochloric acid, and the whole was extracted with methylene chloride. An organic layer was taken out and dried with magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resultant solid was purified by means of silica gel column chromatography to obtain 2.2 g of a pale yellow solid (35% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 622 with respect to a molecular weight of 622.24.

後処理

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 48 hours in an argon atmosphere
  3. customAfter the completion of the reaction
  4. filtrationthe resultant was filtered
  5. additionThe filtrate was poured into 1 L of 10-mass % hydrochloric acid
  6. extractionthe whole was extracted with methylene chloride
  7. dry with materialdried with magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant solid was purified by means of silica gel column chromatography

出典と根拠

ORDレコード
ord-b14732359192416fbddfeac0cfd11b95
出典データセット
uspto-grants-2010_11
特許番号
US07833632B2

反応ノート

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